Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
  • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

• the present invention has for an object agents for coloring keratin fibers, for example wool, furs and particularly human hair, and which contain thiazoliumazo dyes.
• Two coloring methods are usually used for the color-changing treatment of keratin fibers.
• the coloring is accomplished with oxidative or permanent colorants by use of a mixture of different developers and couplers and an oxidant.
• a direct (non-oxidative) dye if the coloring result is to be adjusted or special coloring effects are to be achieved.
• the second method involves the exclusive use of direct dyes which in an appropriate carrier composition are applied to the fibers. This method is easy to apply, very gentle and causes only minor damage to the keratin fibers.
• the direct dyes used for this purpose are subject to many requirements.
• the colorations obtained are required to exhibit good light stability, acid resistance and abrasion resistance.
• Direct dyes are also used in various ways as color shade-adjusting aids in oxidative colorants.
• a direct (non-oxidative) colorant for keratin fibers it is usually necessary to use a combination of different non-oxidative dyes. Because the selection of dyes that can be used in colorants for keratin fibers is limited, a need for such dyes continues to exist.
• the present invention has for an object an agent for coloring keratin fibers, particularly human hair, said agent being characterized in that it contains at least one thiazoliumazo dye of general formula (I)
• R1 stands for a saturated or unsaturated (C 1 -C 12 )-alkyl group, a (C 1 -C 12 )-alkyl group substituted with a halogen atom (F, Cl, Br, I), a hydroxy-(C 1 -C 12 )-alkyl group, a (C 1 -C 6 )-alkoxy-(C 1 -C 12 )-alkyl group, an amino-(C 1 -C 12 )-alkyl group, a (C 1 -C 6 )-alkylamino-(C 1 -C 12 )-alkyl group, a di(C 1 -C 6 )-alkylamino-(C 1 -C 12 )-alkyl group, a cyano-(C 1 -C 12 )-alkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted benzyl group; R
• R1 stands for a saturated or unsaturated (C 1 -C 12 )-alkyl group
• R4 stands for a saturated or unsaturated (C 1 -C 12 )-alkyl group being particularly preferred
• a ⁇ preferably stands for a chloride, bromide, iodide, hydrogen sulfate, sulfate, toluenesulfonate, monomethylsulfate, hexafluorophosphate, hexafluoroantimonate, tetrafluoroborate, tetraphenylborate, formate, acetate or propionate among which the chloride ion, bromide ion, monomethylsulfate ion and acetate ion are particularly preferred.
• Suitable compounds of general formula (I) are, for example, the following: 3-methyl-2- ⁇ [[4-[methyl(phenylmethyl)amino]phenyl]azo ⁇ thiazolium chloride, 3-methyl-2- ⁇ [4-[methyl(phenylmethyl)amino]phenyl]azo ⁇ thiazolium bromide, 3-methyl-2- ⁇ [4-[methyl(phenylmethyl)amino]phenyl]azo ⁇ thiazolium monomethylsulfate, 3-methyl-2- ⁇ [4-[methyl(phenylmethyl)amino]phenyl]azo ⁇ thiazolium acetate, 3,4-dimethyl-2- ⁇ [4-[methyl(phenylmethyl)aminophenyl]azo ⁇ thiazolium chloride, 3,4-dimethyl-2- ⁇ [4-[methyl(phenylmethyl)aminophenyl]azo ⁇ thiazolium bromide, 3,4-dimethyl-2- ⁇ [4-[methyl(phenylmethyl)aminopheny
• Particularly preferred compounds of formula (I) are: 3-methyl-2-[(4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium chloride, 3-methyl-2-[(4-[methyl(phenylmethyl)amino]phenyl]azo]thiazolium bromide, 3-methyl-2-[(4-[methyl(phenylmethyl)amino]-phenyl]azo]thiazolium monomethylsulfate, 3-methyl-2-[(4-[methyl(phenylmethyl)amino]-phenyl]azo]thiazolium acetate, 3,4-dimethyl-2- ⁇ [4-[methyl(phenylmethyl)amino]phenyl]azo ⁇ thiazolium chloride, 3,4-dimethyl-2- ⁇ [4-[methyl(phenylmethyl)amino]phenyl]azo ⁇ thiazolium bromide, 3,4-dimethyl-2- ⁇ [4-[methyl(phenylmethyl)amino]phenyl]
• the colorant of the invention contains the compounds of formula (I) in an amount from 0.01 to 10 wt. % and particularly from 0.1 to 8 wt. %.
• the colorant of the invention can additionally contain other known direct dyes from the group consisting of nitro dyes, azo dyes, anthraquinone dyes and triphenylmethane dyes as well as natural direct dyes (for example henna and indigo) alone or in admixture with one another, for example 1,4-bis[(2-hydroxyethyl)amino]-2-nitrobenzene, 1-(2-hydroxyethyl)amino-2-nitro-4-[di(2-hydroxyethyl)amino]benzene (HC Blue No. 2), 1-amino-3-methyl-4-[(2-hydroxyethyl)amino]-6-nitrobenzene (HC Violet No.
• direct dyes from the group consisting of nitro dyes, azo dyes, anthraquinone dyes and triphenylmethane dyes
• natural direct dyes for example henna and indigo
• the colorant of the invention can contain the afore-said direct dyes in a total amount from about 0.01 to 4 wt. %, the total amount of dyes contained in the colorant of the invention being from about 0.01 to 10 wt. % and particularly from 0.1 to 8 wt. %.
• oxidation precursors for example o,p,m-phenylenediamines, o,p,m-aminophenols, diphenols or 4,5-diaminopyrazoles and suitable oxidants.
• the colorant can contain each of these additional developers and couplers in a total amount from about 0.01 to 20 wt. %, preferably from about 0.1 to 10 wt. % and particularly from 0.1 to 5 wt. %.
• the colorant of the invention can be in the form of, for example, a solution, particularly an aqueous or aqueous-alcoholic solution, or a cream, a gel, a surfactant-containing foaming solution (shampoo, aerosol), an emulsion or some other water-containing carrier suitable for use on hair.
• the colorant of the invention can also be in the form of pellets, granulate or powder which before use are dissolved in an aqueous preparation, for example water or an aqueous oxidant preparation.
• the composition of these agents consists of a mixture of the dye component with the additives usually employed for such preparations.
• Common additives to solutions, creams, emulsions or gels are, for example, solvents such as water, the lower aliphatic monohydric or polyhydric alcohols, the esters and ethers thereof, for example alkanols, particularly those with 1 to 4 carbon atoms, for example ethanol, propanol, isopropanol, butanol, isobutanol, dihydric and trihydric alcohols, particularly those with 2 to 6 carbon atoms, for example ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,2,6-hexanetriol, glycerol, diethylene glycol, dipropylene glycol, polyalkylene glycols such as triethylene glycol, polyethylene glycol, tripropylene glycol, polypropylene glycol, the lower alkyl ethers of polyhydric alcohol
• the colorant of the invention can contain wetting agents or emulsifiers from the classes of anionic, cationic, amphoteric, nonionic or zwitterionic surface-active substances, for example fatty alcohol sulfates, ethoxylated fatty alcohol sulfates, alkylsulfonates, alkylbenzenesulfonates, ⁇ -olefinsulfonates, alkyltrimethylammonium salts, alkylbetaines, ethoxylated fatty alcohols, ethoxylated nonylphenols, fatty alkanolamides, ethoxylated fatty esters, fatty alcohol polyglycol ether sulfates, alkylpolyglucosides, thickeners such as the higher fatty alcohols, starch, cellulose derivatives, vaselines, paraffin oil, fatty acids and other fat constituents in emulsified form, water-soluble polymeric thickeners such as the natural gums, gu
• the said constituents are used in amounts normally employed for such purposes, for example the wetting agents and emulsifiers at a concentration from about 0.1 to 30 wt. %, the thickeners in an amount from about 0.1 to 30 wt. % and the hair-care agents at a concentration from about 0.1 to 5 wt. %.
• the colorant of the invention has a pH from about 3 to 11 and preferably from about 3 to 10.
• Both organic and inorganic acids or bases are suitable for adjusting the pH according to the invention.
• Suitable acids are, in particular, the following: ⁇ -hydroxycarboxylic acids, for example glycolic, lactic, tartaric, citric and malic acid; ascorbic acid; gluconolactone, acetic acid, hydrochloric acid and phosphoric acid as well as mixtures of said acids.
• Suitable bases are, in particular, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, sodium phosphate, borax (Na 2 B 4 O 7 ⁇ 10H 2 O), disodium hydrogen phosphate, sodium hydroxide, potassium hydroxide, ammonia and other organic amines such as monoethanolamine, diethanolamine, triethanolamine, N-methyl-N-ethanolamine, N-methyl-N,N-diethanolamine, 2-(2-hydroxyethoxy)ethanolamine, di-2-(2-hydroxyethoxy)ethanamine and tri-2-(2-hydroxyethoxy)ethanamine.
• An alkaline pH is preferably obtained by adjustment with ammonia and/or monoethanolamine.
• the colorant of the invention is used by applying to the hair an amount of said colorant sufficient for hair dyeing namely about 30 to 120 grams depending on the length of the hair, the colorant then being allowed to act on the hair at about 15 to 50° C., preferably at 30 to 40° C., for about 1 to 60 min, preferably for 5 to 30 min, after which the hair is thoroughly rinsed with water, optionally washed with a shampoo, and then dried.
• the afore-described colorant can also contain natural or synthetic polymers or modified polymers of natural origin commonly used in cosmetic agents and which fix the hair at the same time they color it. Such agents are generally referred to as tinting fixatives or dye fixatives.
• Synthetic polymers that are suitable for this purpose in the cosmetic field are, for example, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and polyacrylic compounds such as polyacrylic acid and polymethacrylic acid, basic polymers of the esters of polyacrylic acid or of polymethacrylic acid and aminoalcohols, for example the salts or quaternization products thereof, polyacrylonitrile, polyvinyl acetates and the copolymers of such compounds, for example polyvinylpyrrolidone-vinyl acetate.
• Suitable natural polymers or modified natural polymers are, for example, chitosan (deacetylated chitin) and chitosan derivatives.
• the agent of the invention can contains the afore-said polymers in an amount usually employed in such agents, particularly in an amount from about 1 to 5 wt. %.
• the pH of the tinting fixative or dye fixative of the invention is preferably about 4 to 10.
• the hair colorant with additional fixative action is applied in the known and usual manner by moistening the hair with the fixative, arranging (setting) the hair into a hairdo and then drying.
• the compounds of formula (I) of the invention make it possible to achieve an outstanding, uniform, intense, brilliant and very long-lasting blue to violet coloration of keratin fibers, particularly of human hair, under gentle and skin-compatible conditions, said colorant showing excellent light stability and unusual resistance to perspiration.
• the dyes in and of themselves are known.
• the dyes of formula (I) can be prepared by methods analogous to the known methods of preparation, for example via azo coupling of 2-aminothiazole derivatives with N-benzylaminophenyl derivatives followed by quaternization, or via oxidative condensation of thiazolone hydrazones with N-benzylaminophenyl derivatives.
• the dye solution was adjusted to the desired pH by addition of ammonia or citric acid.
• the hair was dyed by applying to it an amount of colorant sufficient for hair dyeing and uniformly distributing the colorant with a brush. After a treatment time of 30 min at 40° C., the hair was rinsed with lukewarm water, washed with a shampoo, rinsed with lukewarm water and then dried.
• the dye solution was adjusted to the desired pH by addition of ammonia or citric acid.
• the hair was dyed by applying to it an amount of colorant sufficient for hair dyeing and uniformly distributing the colorant with a brush. After a treatment time of 30 min at 40° C., the hair was rinsed with lukewarm water, washed with a shampoo, rinsed with lukewarm water and then dried.
• the dye solution was adjusted to the desired pH by addition of ammonia or citric acid.
• the hair was dyed by applying to it an amount of colorant sufficient for hair dyeing and uniformly distributing the colorant with a brush. After a treatment time of 30 minutes at 40° C., the hair was rinsed with lukewarm water, washed with a shampoo, rinsed with lukewarm water and then dried.
• the dye solution was adjusted to the desired pH by addition of ammonia or citric acid.
• the hair was dyed by applying to it an amount of colorant sufficient for hair dyeing and uniformly distributing the colorant with a brush. After a treatment time of 30 minutes at 40° C., the hair was rinsed with lukewarm water, washed with a shampoo, rinsed with lukewarm water and then dried.
• the indicated L*a*b* color values were determined with the aid of a Chromameter II color-measuring instrument supplied by Minolta.
• the L-value stands for brightness (namely the lower the L-value, the higher is the color intensity)
• the a-value is a measure of the red content of the color (namely the higher the a-value, the higher is the red content).
• the b-value is a measure of the blue content of the color, namely the more negative the b-value the higher is the blue content.

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Citations (5)

• 2004
  • 2004-02-21 DE DE102004008603A patent/DE102004008603A1/de not_active Withdrawn
  • 2004-11-16 US US10/589,369 patent/US7537620B2/en active Active
  • 2004-11-16 EP EP04821679A patent/EP1727514A1/de not_active Withdrawn
  • 2004-11-16 WO PCT/EP2004/012983 patent/WO2005079733A1/de not_active Application Discontinuation
  • 2004-11-16 BR BRPI0418387-8A patent/BRPI0418387A/pt not_active Application Discontinuation
  • 2004-11-16 JP JP2006553453A patent/JP2007523101A/ja not_active Withdrawn

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